'Click' ligand for 'click' chemistry: (1-(4-methoxybenzyl)-1-H-1,2,3-triazol-4-yl)methanol (MBHTM) accelerated copper-catalyzed [3+2] azide-alkyne cycloaddition (CuAAC) at low catalyst loading

摘要

Readily accessible, cost effective, remarkably stable and easily tunable 1,2,3-triazole based ligand, (1-(4-methoxybenzyl)-1-H-1,2,3-triazol-4-yl)methanol (MBHTM) synthesized itself by 'click' chemistry shown to promote the dramatic rate enhancement of copper catalyze azide-alkyne cycloaddition (CuAAC) at low catalyst loading to give diverse 1,4-disustituted 1,2,3-triazoles in high to excellent yields under mild conditions. Using higher catalyst and ligand loading, excellent and 49% yield of the corresponding 1,2,3 triazole product could be obtained within less than an hour and few minutes, respectively, indicating the feasibility of the reaction for the development of rapid 'click' protocol. (C) 2015 Elsevier Ltd. All rights reserved.